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Urea → 4-(3,5-Bis-trifluoromethylphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid amide

HRID 393683
Notes
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Reaction equation

HRID 393683 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[CH:6]=O.[C:17]([NH2:23])(=[O:22])[CH2:18][C:19]([CH3:21])=O.[NH2:24][C:25]([NH2:27])=[O:26].B(F)(F)F.CCOCC>[Cu](Cl)Cl.C1COCC1.CC(O)=O>[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([CH:6]2[C:18]([C:17]([NH2:23])=[O:22])=[C:19]([CH3:21])[NH:27][C:25](=[O:26])[NH:24]2)[CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 1176UreaHCID 8000Boron trifluoride etherateHCID 80077AcetoacetamideHCID 1362473,5-Bis(trifluoromethyl)benzaldehyde

Product 1

HCID 865860054-(3,5-Bis-trifluoromethylphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid amideYield 36.2%

Reagents, catalysts & solvents 3

HCID 24014Cupric ChlorideCatalyst
HCID 176Acetic AcidSolvent
HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 3,5-bis(trifluoromethyl)benzaldehyde (2.42 g, 10.0 mmol), acetoacetamide (1.01 g, 10.0 mmol), urea (0.90 g, 15.0 mmol), copper chloride (0.1 g, 1.0 mmol), boron trifluoride etherate (0.09 mL), AcOH (0.04 mL), and THF (20 mL) was heated at 65° C. for 18 h and cooled to room temperature. The resulting precipitates were collected by vacuum filtration, washed with THF, and air dried to give the title compound as an off-white solid(1.33 g, 36%).

Workup

  1. temperaturecooled to room temperature
  2. customThe resulting precipitates
  3. filtrationwere collected by vacuum filtration
  4. washwashed with THF, and air
  5. customdried

Sources & evidence

ORD record
ord-b6dad4d14dd3474a9e23c7ce406e1919
Source dataset
uspto-grants-2004_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06809102B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes